Ivan gubelmann



Patented. Apr. 5, 1927.,

UNITED STATES rml..

PATENT OFFICE.

IVAN GUBELMANN, HENRY J. WEILAND, 4ANI) OTTQ STALLIANN, 0F SOUTH/HIL- WAUKEE, WISCONSIN, iSSIGNOB'S T0 TEE NEWPORT COIPANY, A CORPORATION F DELAWARE.

This invention `relates tothe method of manufacture of guaiacol through the decomposition of'diazQ-o-aniso1. This decomposition is ordinarily carried out in the presence `5 of sulfuric acid and its salts, such as cop'- per sulphate, sodium sulphate, ammonium sulphate and others. 'It was found' that no` method-is described in the literature which gives a yield over 85% of theory. A -careful study of the reaction revealed the fact- -that the use of sulphuric acid alone, or together with its salts, decomposes part-.of the material through the formation of by, products, which naturally lower the yield of l5 the'guaiacol and also its purity.

This invention lfurnishes an `improvement 'for the manufacture or' guaiacol, which reduces the :formation of b -products to a minimum and by which yields as high as 95% of theory are obtained. We have discoveredthat the addition of phosphoric acid orits salts to the reacting substances during decomposition furnishes the most favorable conditions. We prefer thense of tri-sodium phosphate for the reason that the sulphuric acid contained in the diazo solution, which is .continuously added to the decomposition mass, is neutralized thereby, butv copper ,phosphate may also .be used. .The amountv e0 of tarry products formed during the decomposition is very small and the formation of volatile by-products is practically avoided.-

Itis obvious that-phosphoric acid in place of thetri-sodiump osphat'e,cou,ld beadded A3 5 duringthe decomposition, if the-sulphuric -acid -werev otherwise? neutralized, asby the.

l' addition d ash Causti'csoda, 0 1' any suitable neutralizing agen@ Y v To -illustrate how the formation of guaia- 40 colis accomplished, the' following example is given:

123 grams of orthoanisidine are dissolved y j ofte-opper sulphate and simultaneousl neuan grams of Water and 890` grams ojice are j lof ati'isodium p osp'hate solution at such a r'nocass or mme etra'racor..

ppliuation tiled September 80, 1925. Serial No. 59,735.

temperature of below 5 C. -The diazo solutlon thus prepared is run slowlyv into a boiling solutlon of 260 grams of crystallized 5c copper sulphate, 42 grams of vtri-sodium phosphate and 31.5 grams of sulphuric acid B. in 260 grams of water. Heat is applied tothe reaction vessel at such a rate as to keep the temperature in the reaction ves@ 55 sel betweenl 102 andf105 C.' During the addition of the diazo solution, a solution of 52.5 grams of tri-sodium phos hate in 2100 grams of Water is slowly ad ed. 'The decomposition. of :the diazo-o-anisol ytakes et place. The yield of guaiacol in the condensatewill aproach`95% of the theoretical. It will e understood that the rocess above cited may be varied: without la ecting the result obtained., For instance,l instead 65 y of diazotzing in sulphuric acid solution the dia-zotization may be effected in phosphoric acid solution. The im ortant point -to be observed is not to have reesulphuric i during `the decomposition the Y e claim as our invention: 1. The process o f making guaiacol which Y consists in decomposing diazo-o-anisol in the '30 -prlesence of phosphoric'acid salts and copper feats. i

2. The process of making guaiacol which 7 consists in decomposing. diazo-o-anisol in the f sulphate.

' ,3.- The process of making guaiacol which cntaininglfr'ee sulphuric acid to a solution tralizingthesul 'huric Iacid by the a dition 111156thatno fr@ Sulphm'icaeid is preseg'tiin i f 'aidissolved mais grams of waar, stuitte 'faceta p esence of copper phosphate and copper'35 consists lin adding a-diazo-oianisol solution` g naamw 4. The process of making guaiaco which the presence of a phosphoric acid salt, but consists in adding a diazo-ofanisol solution in the absence of :free sulphuric acid. 10 containing free mineral acid to a solution In testimony whereof We have hereunto of copper sulphate and vsimultaneously neusubscribed our names.

5 tralizinor the mineral acid by the addition 'of IVAN GUBELMANN.

a trisodium phosphate solution. v

5., The process of making guaiacol which HENRY J. WEILAND.

' OTTO STALLMANN.

consists in decomposing diazo-o-anisol in 

